Default HTG hotel image

Middle Haddam Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Middle Haddam vacation rentals

View from property

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (184 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is AED 465
AED 873 total
includes taxes & fees
7 Sep - 8 Sep
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Smart TV, fireplace, books, music library

2. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is AED 459
AED 951 total
includes taxes & fees
29 Sep - 30 Sep
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Property grounds

3. Lakeview Carriage House with Spectacular Sunset Views

Lakeview Carriage House with Spectacular Sunset Views
Lake Pocotopaug
10.0 out of 10, Exceptional, (19 reviews)
"Clean, quiet, beautiful surroundings and a great host"
United States
Jennifer J.
The price is AED 551
AED 1,185 total
includes taxes & fees
7 Sep - 8 Sep
Lakeview Carriage House with Spectacular Sunset Views
Dining

4. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
8.8 out of 10, Excellent, (5 reviews)
The price is AED 562
AED 1,192 total
includes taxes & fees
24 Sep - 25 Sep
2BR Apartment Near Wesleyan 102
Exterior

5. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.6 out of 10, Exceptional, (41 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is AED 716
AED 1,163 total
includes taxes & fees
1 Sep - 2 Sep
Walk To Goodspeed Opera House!
Property grounds

6. #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
The price is AED 782
AED 1,531 total
includes taxes & fees
20 Sep - 21 Sep
#24 *Serenity* A Lakefront Cottage Retreat
Coffee/tea maker, fridge, microwave, oven

7. “3BR Home Near Wesleyan & Downtown Middletown

“3BR Home Near Wesleyan & Downtown Middletown
Washington Street Historic District
7.8 out of 10, Good, (6 reviews)
"Nice place"
United States
Jousette C.
“3BR Home Near Wesleyan & Downtown Middletown
Dining

8. 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201
Washington Street Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Clean apartment plenty of parking"
United States
Rebecca P.
The price is AED 632
AED 1,384 total
includes taxes & fees
3 Sep - 4 Sep
3 BR Apartment Near Wesleyan 201
Exterior

9. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Very nice! Clean and had everything you would need for a few nights away from home. I book again. "
United States
ALRUNDUS L.
The price is AED 433
AED 1,086 total
includes taxes & fees
15 Sep - 16 Sep
All New 1BR with tons of Charm
1 bedroom, iron/ironing board, WiFi, bed sheets

10. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 433
AED 1,086 total
includes taxes & fees
1 Sep - 2 Sep
Once the old Schools house now a newly furnished Apartment
Interior

11. Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance.
Marlborough
The price is AED 612
AED 1,835 total
includes taxes & fees
1 Sep - 2 Sep
Cozy basement apartment with private bathroom, kitchen and entrance.
Exterior

12. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
The price is AED 433
AED 1,086 total
includes taxes & fees
1 Sep - 2 Sep
All New Studio apartment in center of town
Smart TV, offices, computer monitors

13. Central Chic Pad - with Free Parking, Heat & AC

Central Chic Pad - with Free Parking, Heat & AC
Manchester
9.6 out of 10, Exceptional, (7 reviews)
"Great stay. Gas stove was a highlight!"
United States
Domenic
The price is AED 317
AED 779 total
includes taxes & fees
1 Sep - 2 Sep
Central Chic Pad - with Free Parking, Heat & AC
Property grounds

14. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
8.8 out of 10, Excellent, (53 reviews)
"Stayed for a wedding. Perfect stay!"
United States
Christine M.
The price is AED 350
AED 927 total
includes taxes & fees
2 Sep - 3 Sep
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
TV

15. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
The price is AED 433
AED 1,086 total
includes taxes & fees
20 Sep - 21 Sep
Newly Remodeled 1-BR Close to Everything yet Very Private
Property grounds

16. Humble Abode #2

Humble Abode #2
Manchester Center
10.0 out of 10, Exceptional, (4 reviews)
"the place was clean bed was nice"
United States
Jonathan
The price is AED 441
AED 580 total
includes taxes & fees
24 Sep - 25 Sep
Humble Abode #2
1 bedroom, desk, iron/ironing board, travel crib

17. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (55 reviews)
"We enjoyed our stay"
United States
JM B.
The price is AED 463
AED 881 total
includes taxes & fees
28 Sep - 29 Sep
1-bedroom cottage with Grove Beach 🏖️ access.
Coffee/tea maker, fridge, microwave, oven

18. Private Apt in Middletown-Wesleyan 101

Private Apt in Middletown-Wesleyan 101
Washington Street Historic District
7.0 out of 10, Good, (4 reviews)
"Very clean. No frills."
United States
Kristoph
The price is AED 547
AED 1,276 total
includes taxes & fees
3 Sep - 4 Sep
Private Apt in Middletown-Wesleyan 101
Coffee/tea maker, fridge, microwave, oven

19. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Very nice cozy cottage, the host was very friendly"
United States
Wink V.
The gardners Cottage 1 mile from long Island Sound - pet friendly
Beach nearby

20. Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks

Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Coventry Lake
9.0 out of 10, Wonderful, (48 reviews)
"The property was clean and accommodating."
United States
Ann Marie T.
The price is AED 350
AED 927 total
includes taxes & fees
2 Sep - 3 Sep
Lake - PetsOK - Wi-Fi - W&D - Fire Pit - Kayaks
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middle Haddam Hotel Reviews

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

8/10 Good
"Breakfast needs some work. Other than that, this place served its purpose."
Jonathan 1-night trip
Posted 9 hours ago
Clarion Inn North Haven - New Haven North

Frequently asked questions

Are there vacation rentals in Middle Haddam?

Yes, we have vacation rentals near the most popular local attractions in Middle Haddam, or you can go with a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental that Middle Haddam has to offer?

New Madison beach house - Ocean front- Great views- booking Summer 2026: Visitors like this Middle Haddam vacation home rental. It is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What can I see and do in Middle Haddam?

While exploring the area, visit family-friendly sights like Brownstone Exploration & Discovery Park, or get outside and enjoy nature at Connecticut River. In the larger area, you’ll find Hurd State Park and Machimoodus State Park.

What are vacation rentals like in Middle Haddam?

Vacation rentals are privately owned properties you can reserve for a few days or a quick weekend in Middle Haddam. Vacation rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a small group gathering.